Cyamemazine

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Cyamemazine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, IM, IV
ATC code	N05AA06 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	10-70%
Metabolism	Hepatic
Elimination half-life	10 hours
Excretion	Urine
Identifiers
	IUPAC name 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile;
CAS Number	3546-03-0 ;
PubChem CID	62865;
IUPHAR/BPS	84;
DrugBank	DB09000 ;
ChemSpider	56597 ;
UNII	A2JGV5CNU4;
KEGG	D07307 ;
ChEMBL	ChEMBL2104153 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C19H21N3S
Molar mass	323.46 g/mol
3D model (JSmol)	Interactive image;
	SMILES N#Cc2cc1N(c3c(Sc1cc2)cccc3)CC(C)CN(C)C;
	InChI InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3 ; Key:SLFGIOIONGJGRT-UHFFFAOYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class which was introduced by Theraplix in France in 1972 and later in Portugal as well.^[1]^[2]^[3]^[4] It is used for the treatment of schizophrenia and, especially, for psychosis-associated anxiety, due to its unique anxiolytic efficacy.^[5]^[6]

Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile of dopamine, α₁-adrenergic, H₁, and mACh receptor antagonism,^[7] it additionally produces potent blockade of several serotonin receptors, including 5-HT_2A, 5-HT_2C, and 5-HT₇.^[7]^[8]^[9]^[10] These actions have been implicated in cyamemazine's anxiolytic effects (5-HT_2C) and lack of extrapyramidal side effects (5-HT_2A),^[7]^[8] and despite being classified as a typical, it actually behaves like an atypical antipsychotic.^[11]

References

↑ Index nominum, international drug ... - Google Books.
↑ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 534. ISBN 0-412-46630-9.
↑ Pharmaceutical manufacturing ... - Google Books.
↑ Bret P, Bret MC, Queuille E (April 2009). "[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals]". L'Encéphale (in French). 35 (2): 129–38. doi:10.1016/j.encep.2008.03.007. PMID 19393381.
↑ "Stahl's Essential Psychopharmacology - Cambridge University Press".
↑ Bourin M, Nic Dhonnchadha BA, Claude Colombel M, Dib M, Hascoët M (September 2001). "Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice". Behavioural Brain Research. 124 (1): 87–95. doi:10.1016/S0166-4328(01)00238-8. PMID 11423169.
↑ ^7.0 ^7.1 ^7.2 Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M (February 2003). "Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes". Biochemical Pharmacology. 65 (3): 435–40. doi:10.1016/S0006-2952(02)01515-0. PMID 12527336.
↑ ^8.0 ^8.1 Alvarez-Guerra M, d'Alché-Birée F, Wolf WA, Vargas F, Dib M, Garay RP (January 2000). "5-HT3- and 5-HT2C-antagonist properties of cyamemazine: significance for its clinical anxiolytic activity". Psychopharmacology. 147 (4): 412–7. doi:10.1007/s002130050010. PMID 10672635.
↑ Alvarez-Guerra M, Hameg A, Bayle F, Dib M, Garay RP (November 2002). "5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle". European Journal of Pharmacology. 454 (2–3): 235–9. doi:10.1016/S0014-2999(02)02489-5. PMID 12421652.
↑ Benyamina A, Arbus C, Nuss P, Garay RP, Neliat G, Hameg A (January 2008). "Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes". European Journal of Pharmacology. 578 (2–3): 142–7. doi:10.1016/j.ejphar.2007.09.025. PMID 17936750.
↑ Peinado J, Hameg A, Garay RP, Bayle F, Nuss P, Dib M (February 2003). "Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine". Naunyn-Schmiedeberg's Archives of Pharmacology. 367 (2): 134–9. doi:10.1007/s00210-002-0665-4. PMID 12595954.

[urlIndex_nominum,_international_drug_..._-_Google_Books-1] Index nominum, international drug ... - Google Books.

[isbn0-412-46630-9-2] David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 534. ISBN 0-412-46630-9.

[urlPharmaceutical_manufacturing_..._-_Google_Books-3] Pharmaceutical manufacturing ... - Google Books.

[pmid19393381-4] Bret P, Bret MC, Queuille E (April 2009). "[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals]". L'Encéphale (in French). 35 (2): 129–38. doi:10.1016/j.encep.2008.03.007. PMID 19393381.

[urlStahls_Essential_Psychopharmacology_-_Cambridge_University_Press-5] "Stahl's Essential Psychopharmacology - Cambridge University Press".

[pmid11423169-6] Bourin M, Nic Dhonnchadha BA, Claude Colombel M, Dib M, Hascoët M (September 2001). "Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice". Behavioural Brain Research. 124 (1): 87–95. doi:10.1016/S0166-4328(01)00238-8. PMID 11423169.

[pmid12527336-7] 7.0 ^7.1 ^7.2 Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M (February 2003). "Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes". Biochemical Pharmacology. 65 (3): 435–40. doi:10.1016/S0006-2952(02)01515-0. PMID 12527336.

[pmid10672635-8] 8.0 ^8.1 Alvarez-Guerra M, d'Alché-Birée F, Wolf WA, Vargas F, Dib M, Garay RP (January 2000). "5-HT3- and 5-HT2C-antagonist properties of cyamemazine: significance for its clinical anxiolytic activity". Psychopharmacology. 147 (4): 412–7. doi:10.1007/s002130050010. PMID 10672635.

[pmid12421652-9] Alvarez-Guerra M, Hameg A, Bayle F, Dib M, Garay RP (November 2002). "5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle". European Journal of Pharmacology. 454 (2–3): 235–9. doi:10.1016/S0014-2999(02)02489-5. PMID 12421652.

[pmid17936750-10] Benyamina A, Arbus C, Nuss P, Garay RP, Neliat G, Hameg A (January 2008). "Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes". European Journal of Pharmacology. 578 (2–3): 142–7. doi:10.1016/j.ejphar.2007.09.025. PMID 17936750.

[pmid12595954-11] Peinado J, Hameg A, Garay RP, Bayle F, Nuss P, Dib M (February 2003). "Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine". Naunyn-Schmiedeberg's Archives of Pharmacology. 367 (2): 134–9. doi:10.1007/s00210-002-0665-4. PMID 12595954.

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v t e Antipsychotics (neuroleptics) (N05A)
Typical	Benzamides: Levosulpiride • Nemonapride • Sulpiride • Sultopride • Tiapride • Veralipride; Butyrophenones: Azaperone • Benperidol • Bromperidol • Droperidol • Fluanisone • Haloperidol • Lenperone • Moperone • Pipamperone • Spiperone • Timiperone • Trifluperidol; Diphenylbutylpiperidines: Clopimozide • Fluspirilene • Penfluridol • Pimozide; Phenothiazines: Acepromazine • Acetophenazine • Butaperazine • Carphenazine • Chloracizine • Chlorproethazine • Chlorpromazine • Cyamemazine • Dixyrazine • Fluacizine • Fluphenazine • Levomepromazine/Methotrimeprazine • Mesoridazine • Perazine • Periciazine • Perphenazine • Piperacetazine • Pipotiazine • Prochlorperazine • Promazine • Promethazine • Propiomazine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioproperazine • Thioridazine • Trifluoperazine • Triflupromazine; Thioxanthenes: Chlorprothixene • Clopenthixol • Flupentixol • Thiothixene • Zuclopenthixol; Tricyclics: Amoxapine • Butaclamol • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin • Trimipramine; Others: Prothipendyl
Atypical	Benzamides: Amisulpride • Remoxipride; Butyrophenones: Cinuperone • Setoperone; Benzo(iso)oxazole piperidines: Iloperidone • Ocaperidone • Paliperidone • Risperidone; Benzo(iso)thiazole piperazines: Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone; Diphenylbutylpiperazines: Amperozide; Phenylpiperazines: Aripiprazole • Bifeprunox • Elopiprazole • Umespirone; Tricyclics: Asenapine • Carpipramine • Clocapramine • Clotiapine • Clozapine • Fluperlapine • Gevotroline • Metitepine/Methiothepin • Mosapramine • NDMC • Olanzapine • Piquindone • Quetiapine • Tenilapine • Zotepine; Others: Blonanserin • Cariprazine • Molindone • Pimavanserin • Roxindole • Sarizotan • Sertindole • Spiramide
Others	Azacyclonol • Cannabidiol • D-Cycloserine • Lithium • Mifepristone • Oxypertine • Reserpine • Rimcazole • Secretin • Talnetant • Tetrabenazine • Vabicaserin
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III Template:Psychology navs

Cyamemazine

Overview

See also

References

Navigation menu

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, IM, IV
ATC code	N05AA06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	10-70%
Metabolism	Hepatic
Elimination half-life	10 hours
Excretion	Urine
Identifiers
IUPAC name 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile
CAS Number	3546-03-0^Y
PubChem CID	62865
IUPHAR/BPS	84
DrugBank	DB09000^N
ChemSpider	56597^Y
UNII	A2JGV5CNU4
KEGG	D07307^Y
ChEMBL	ChEMBL2104153^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₉H₂₁N₃S
Molar mass	323.46 g/mol
3D model (JSmol)	Interactive image
SMILES N#Cc2cc1N(c3c(Sc1cc2)cccc3)CC(C)CN(C)C
InChI InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3^Y Key:SLFGIOIONGJGRT-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)